Related Experiment Video
Updated: Feb 27, 2026
09:36
Author Spotlight: Discovering New Alkaloids in Plants with Advanced Mass Spectrometry Techniques
Published on: March 8, 2024
1.5K
Amaryllidaceae alkaloids: Absolute configuration and biological activity
Alessio Cimmino1, Marco Masi1, Marco Evidente1
1Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte S. Angelo, Napoli, Italy.
Chirality
|June 27, 2017
Summary
Amaryllidaceae alkaloids, like galanthamine for Alzheimer's disease, show diverse medicinal uses. This review details their absolute configuration and links it to significant biological activities.
Area of Science:
- Phytochemistry
- Medicinal Chemistry
- Organic Chemistry
Background:
- Amaryllidaceae family plants are sources of alkaloids with diverse biological activities.
- Alkaloid bioactivity is linked to their specific stereochemistry.
- Key examples include galanthamine (Alzheimer's treatment) and anticancer agents like lycorine, narciclasine, and pancratistatine.
Purpose of the Study:
- To review the methods for assigning the absolute configuration of Amaryllidaceae alkaloids.
- To explore the relationship between alkaloid stereochemistry and their observed biological activities.
Main Methods:
- Literature review of studies on Amaryllidaceae alkaloid synthesis and characterization.
- Analysis of stereochemical assignment techniques.
- Correlation of reported biological data with specific alkaloid configurations.
Main Results:
- Several Amaryllidaceae alkaloids possess significant medicinal properties.
- Absolute configuration is critical for the biological efficacy of these compounds.
- Galanthamine's acetylcholinesterase inhibition and the anticancer potential of lycorine analogs are highlighted.
Conclusions:
- Understanding the absolute configuration of Amaryllidaceae alkaloids is crucial for drug development.
- Stereochemistry directly influences the therapeutic potential of these natural products.
- Further research into Amaryllidaceae alkaloids could yield new pharmaceutical agents.
Related Concept Videos
01:16Adrenergic Agonists: Chemistry and Structure-Activity Relationship
4.0K
Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
4.0K
01:26Physical Properties of Amines
4.3K
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
4.3K
01:31Direct-Acting Cholinergic Agonists: Pharmacokinetics
2.0K
Direct-acting cholinergic agonists, such as synthetic choline esters and naturally occurring alkaloids, exert their effects by enhancing the actions of acetylcholine and stimulating the parasympathetic nervous system. Synthetic choline esters share structural similarities with acetylcholine. For example, they have a positively charged quaternary ammonium or onium group, contributing to their hydrophilic characteristics. As a result, they are poorly absorbed in the body through oral...
2.0K
01:07Amines: Introduction
5.9K
Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
5.9K
01:22Direct-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship
2.3K
Cholinergic agonists or cholinomimetics mimic the action of acetylcholine to stimulate the parasympathetic nervous system. They are categorized into direct-acting and indirect-acting agents. The direct-acting cholinergic drugs induce the parasympathetic response by directly binding to the muscarinic or nicotine receptors. In comparison, the indirect-acting cholinergic drugs prevent acetylcholine hydrolysis, indirectly contributing to the extended parasympathetic response.
The direct-acting...
The direct-acting...
2.3K
01:18Basicity of Aromatic Amines
8.2K
The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
8.2K